


The Pool Hall Hustler

by caisha



Series: Well If It's You Asking (Olicity Drabbles) [3]
Category: Arrow (TV 2012), Green Arrow - All Media Types, olicity - Fandom
Genre: AU, Alternate Universe, F/M, Gen, Humor, One Shot, Romance, hustle - Freeform, olicity - Freeform, olicity drabble, pool hall, prompt request
Language: English
Status: Completed
Published: 2015-01-07
Updated: 2015-01-07
Packaged: 2018-03-06 12:04:07
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,808
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3133802
Author URL: https://archiveofourown.org/users/caisha/pseuds/caisha
Summary: <blockquote class="userstuff">
              <p>Tumblr Prompt: "Could you write a short AU one shot where Oliver meets Felicity in a pool hall and she ends up hustling him?"</p><p>So...basically that's what happens. One adorable little pool hall hustle, coming up!</p>
            </blockquote>





	The Pool Hall Hustler

There was a faint siren in the background, but Oliver barely even turned his head in that direction; he pulled his jacket tighter to him to keep the chilly rain from taking up shop on his skin. He walked down the street with impunity, though it was dark and in the middle of the Glades; no one would be bothering him on the streets tonight - the expression he wore was enough to keep anyone away.

Including Laurel, the girlfriend who had just walked out on him after he expressed little interest in moving in with her. It had been three years, but still he felt nothing when she looked at him with such hope on her face when she suggested it. He tried to care, but he was just…gone.

A red sign blazed above him, the only light on the street, and he looked up to see it advertising a pool hall; it was as good a place as any to get drunk on a quiet Wednesday evening, he thought.

He walked in and noted the floors that were covered in chalk dust from the numerous tables lined up, racks of cue sticks pinned against the wall. It had been a number of years since he had played, but he and his father kept a lot of fond memories around the sport and Oliver considered himself quite skilled thanks to skills honed by Tommy in high school.

There were maybe only ten people in the hall, and it was relatively quiet - music was playing, but low volume for a bar; he walked up and sat on a corner stool, bartender coming over and raised his eyebrow at him, silently asking him what he wanted.

"Whiskey, bottle please," Oliver said as he placed down a hundred dollar bill. The man just nodded, showing no surprise; he appreciated that at least here he was just another patron looking to get drunk and maybe play pool - not Oliver Queen, heir to Queen Consolidated and a billionaire who fucked up the only relationship he’d likely ever have.

The faint scent of honeysuckle and sandalwood hit his nose and he turned to see a skittish blonde enter the pool hall, looking incredibly out of place in a red sundress. His eyes locked on hers and she gave him a shy smile, ponytail swaying as she walked up to sit on the other side of the corner next to Oliver.

"Well hello there," Oliver said, trying to ignore the smirk the bartender gave him as he set the bottle of whiskey and glass down in front of him.

She blushed and turned to the bartender, “Hi, um, can I get a cranberry and vodka please?”

Oliver raised his eyebrow this time, noting that she hadn’t said hello to him, “My name is Oliver Queen.” he said, extending his hand.

"Oh! Sorry, Felicity Smoak," she shook his hand gently and he was mesmerized by the smile she gave him.

The bartender set her drink down and Oliver spoke, “Put her drinks on my tab, please.”

"Thanks, I guess," Felicity said softly.

"You can thank me by playing a game of pool with me later," Oliver suggested; he wanted to play a game and there was nothing sexier than teaching a young woman how to play. He could stand behind her and slide his hands down her arms as he showed her how to position the cue. Oliver shook his head, trying to clear the thoughts out. His relationship might be essentially over, but it wasn’t technically over yet - he shouldn’t be thinking about this woman like that right now.

Felicity smiled, “I don’t really know how, isn’t it kind of…hard?”

He chuckled, “Sure, but you’ll have a great teacher. Been playing all my life.” His chest puffed up as he took a sip of his drink, noting she had barely touched hers.

"Well, I’d love to learn if you could teach me. It’s been a really long day, I’d love to unwind," Felicity’s eyes sparked as she looked at him and he grew warm.

He slammed his palm onto the bar, “Well alright then! Let’s get started.”

The bartender, who had since then been silent, spoke up, “Any good pool game starts with a bet.”

Her eyes went wide and she looked to Oliver, “Is that true?”

 Rubbing his neck he responded, “Well yeah I guess, what do you want to bet?”

 She chewed her lip, thinking, “If I beat you, you owe me $100 - but if you win, you get a kiss.”

 ”Well isn’t that interesting,” Oliver teased, “If I didn’t know any better, I’d think you wanted to kiss me.”

 Felicity shook her head coyly, just smiling at him.

 ”I’ll take that bet, but how about if you beat me I’ll give you all the money in my wallet,” Oliver grinned, wondering if she knew how much money he carried around all the time. He was Oliver Queen after all.

 She put her hand out again, “You’ve got yourself a deal, Mr. Queen.”

 He waved her off, “Please. My dad is Mr. Queen, just call me Oliver.” He pulled out his wallet and gave it to the bartender, watching him lock it in the cash register. It was probably foolish to give a stranger access to it, but truth be told it was only a driver’s license and his black AmEx - and a whole lot of cash.

 Felicity hopped off the stool and followed him as he went to the wall to select a stick; he explained all about the importance of choosing one that was a correct height, and making sure the felt was still intact. She listened studiously, smiling sweetly every time he looked at her to be sure she was understanding; and he looked at her a lot.

 ”Okay, I’m probably going to do the break, but go ahead and wrack ‘em up like I taught you,” he said while gesturing to the balls on the green table.

 He watched her as her deft fingers ordered the balls correctly and quickly, “You’re a fast learner - a natural for sure.” Oliver winked at her and she agreed.

 ”That’s what my mom always said, though she’d not be too pleased to see me around here.”

 Her voice washed over him every time she spoke and he lined up the white ball on the other side of the table, trying to concentrate on the break.

 The balls collided in a sharp clinking noise, scattering a fairly good distance - he was glad he hadn’t lost much of his touch since he played last.

 She stumbled on the first few attempts at pocketing the right balls - she had taken stripes, and Oliver was taking it easy on her - she was just too cute to completely annihilate immediately. He wanted this to drag on.

 As he stared off, imagining her lips on his, he heard the snap of a clean shot and looked over to see that Felicity had sunk two balls in one stroke and was bouncing up and down, squealing.

 ”Oh my god! Go me!” 

"Wow! Beginner’s luck is for real," Oliver said, noting how adorable she was with that grin on her face.

 Apparently, beginner’s luck held out for almost the entire game and Oliver had 4 balls left, while Felicity only had the black eight ball.

 ”Wow, this is pretty easy,” she said with surprise in her tone.

 ”Like I said, you’re a natural,” Oliver countered with false brightness; he was beginning to think it was increasingly unlikely that he would be getting that kiss from her tonight.

 He was a little more devious in his next stroke, deliberately blocking her next move from having a chance at sinking the eight ball. He watched her pout as she walked around the table, making a big show of checking the angles. Oliver looked around and saw that most of the people were watching them - including the bartender, who had a smirk on his face for some reason.

 ”Are you sure you haven’t been here before?” He asked tentatively.

 She shook her head, “No way. This is a bad part of town, I just got kind of lost on my way to the main street and then…well, I found you.”

 He returned the smile she gave him and felt reassured.

 Oliver watched her place her left hand on the table gently, fingers barely brushing it as she brought her stick and angled it. He was going to open his mouth to point out that she wasn’t even pointing in the direction of the eight ball when she snapped it back and hit the white ball at an angle.

 The ball spun sharply and as it hit the edge it snapped through the four other balls, hitting the eight ball on the side, causing it to spin and land directly into the pocket.

There was a dead silence as Oliver gaped at the board until a voice spoke in his ear, her lips touching them, “I guess I’m not just a dumb blonde after all, am I Oliver Queen?”

He felt her walk away to the bar, likely to collect her winnings, and all Oliver could do was blink slowly in shock.

"Aw don’t worry boy," one of the patrons said, "She gets everyone the first time around."

There was laughter and it finally snapped him out of it and he spun around to her, “You hustled me!”

She stopped counting the hundred dollar bills that the bartender had pulled from Oliver’s wallet to quirk her head to the side, “It’s entirely possible, but what I do know is that I am now eight hundred dollars richer. Thanks, lover boy.”

He walked up to her slowly, “You lied to me.”

"You were an easy mark, Mr. Queen," she said, her eyes sparkling with mirth.

He smiled at her despite himself. “What are you doing this Friday night?” he asked, surprising himself with the question.

Tilting her head she joked, “Trying to get that kiss anyways, Oliver?”

"Maybe, but mostly it’s that you charmed me from the moment you walked in. And I don’t think it was all an act, Felicity Smoak. Please go out with me, just give me one chance."

She stared at him, trying to decide if he was serious.

"Oh just go out with him honey, maybe you can teach him a thing or two about how to handle a cue stick," one of the patrons yelled loudly, making everyone around them laugh.

She flushed bright red and he brushed her face with the back of his hand, “See? It wasn’t all a game.”

Felicity just smiled and nodded, “Yes, I will go out with you on Friday - but at some point we’re going to have to actually teach  you how to play pool because…honestly, that was embarrassing.”

**Author's Note:**

> Feel free to pester me on tumblr - caishakalianah. I write for both Captain Swan and Olicity <3


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